Cauloside A

Base Information

• Chemical Name: Cauloside A
• CAS No.: 17184-21-3
• Molecular Formula: C35H56 O8
• Molecular Weight: 604.825
• UNII: QW2X5B5L5W
• DSSTox Substance ID: DTXSID80938054
• Nikkaji Number: J38.802E
• Wikidata: Q27106835
• Metabolomics Workbench ID: 135135
• ChEMBL ID: CHEMBL452911
• Mol file: 17184-21-3.mol

Synonyms:3-(alpha-L-arabinopyransoyloxy)-23-hydroxy-olean-12-en-28-oic acid;3-O-(alpha-L-arabinopyranosyl)hederagenin;3-O-arabinopyranosylhederagenin;cauloside A;FJ-2 acid;leontoside A

Chemical Property of Cauloside A

Chemical Property:

• Vapor Pressure: 6.76E-24mmHg at 25°C
• Melting Point: 276-278℃
• Boiling Point: 719.3°C at 760 mmHg
• PKA: 4.63±0.70(Predicted)
• Flash Point: 219.7°C
• PSA: 136.68000
• Density: 1.25g/cm³
• LogP: 4.66930
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 604.39751874
• Heavy Atom Count: 43
• Complexity: 1150

Purity/Quality:

99%, ^*data from raw suppliers

CaulosideA 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)OC6C(C(C(CO6)O)O)O)C)C)C2C1)C)C(=O)O)C
• Isomeric SMILES: C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)CO)O[C@H]6[C@@H]([C@H]([C@H](CO6)O)O)O

Technology Process of Cauloside A

There total 43 articles about Cauloside A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate (171489-59-1) → (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione (171596-36-4)

Guidance literature:

With ammonia; In methanol; at 45 ℃; for 20h;

DOI:10.1016/j.bmcl.2006.10.069

Reference yield:

(1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate (171596-41-1) → (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione (171596-36-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / triethylamine / CHCl₃ / -10 °C

2: 70 percent / NH₃ / methanol / 20 h / 45 °C

With ammonia; triethylamine; In methanol; chloroform;

DOI:10.1016/j.bmcl.2006.10.069

Reference yield:

D-Tryptophan methyl ester (4299-70-1,7303-49-3,22032-65-1) → (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione (171596-36-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 42 percent / TFA / CH₂Cl₂ / 20 °C

2: 93 percent / NaHCO₃ / CHCl₃ / 20 °C

3: 31 percent / methanolic NH₃ / Heating

With ammonia; sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; chloroform; 1: Pictet-Spengler reaction;

DOI:10.1021/jm0300577

upstream raw materials:

diazomethane

HN-saponin P

3-O-<α-L-arabinopyranosyl>hederagenin 28-O-<β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside>

hederagenin 3-O-<β-D-xylopyranosyl-(1-2)-α-L-arabinopyranoside>

Downstream raw materials:

L-(+)-arabinose

hedaragenin

L-arabinose

Refernces

• 1、 Sarikahya, Nazli Boke,Mkouboi, Mohamed Chanfiou,Nalbantsoy, Ayse,Elibol, Murat. "Cytotoxic and immunomodulator potential of hederagenin saponins from Cephalaria tchihatchewii". . p. 216 - 221. Retrieved 2021.
• 2、 Sánchez-Arias, Juan A.,Rabal, Obdulia,Cuadrado-Tejedor, Mar,De Miguel, Irene,Pérez-González, Marta,Ugarte, Ana,Sáez, Elena,Espelosin, Maria,Ursua, Susana,Haizhong, Tan,Wei, Wu,Musheng, Xu,Garcia-Osta, Ana,Oyarzabal, Julen. "Impact of Scaffold Exploration on Novel Dual-Acting Histone Deacetylases and Phosphodiesterase 5 Inhibitors for the Treatment of Alzheimer’s Disease". . p. 638 - 661. Retrieved 2017/03/20.